Since it looks like my conversation with the bible salesgirl story got some laughs I’ve decided to post another story in the same vein. I was in Chicago over the weekend and I decided that since I’m alone in the city in lieu of calling up some friends and hitting the bars I would go to a bar alone and try to make some new friends. And I succeeded, somewhat. I eventually found a decent bar not far from my hotel and as I entered I saw a cute girl sitting alone drinking a red drink from a martini glass. The ensuing conversation went something like this:

Me: Are you drinking a Cosmo?

Cosmo Girl: Yeah, how did you know?

Me: There’s not too many red drinks served in martini glasses. So, what, you’re like a big Sex and the City fan?

Cosmo Girl: Yeah, I love that show, but that’s not the only reason why I drink Cosmos.

Me: (I order a whiskey straight up) Of course not. It’s a tasty drink. (She’s already defending herself to me. This means she cares what I think of her.) I’m not from around here. What’s there to do in this city?

Cosmo Girl: Honestly, I spend most of my time at school. But there’s a lot of great bars in the area. The House of Blues is really cool.

Me: What are you studying?

Cosmo Girl: I’m a marketing major at Loyola.

Me: Interesting. And what do you want to do with that?

Cosmo Girl: I really want to get into advertising. I love art and want to do something creative.

Me: (I get her another Cosmo, she thanks me.) So you’ve probably read like every book Donny Deutsch has ever written, right?

Cosmo Girl: I don’t know who that is.

Me: (brief silence) He’s a big time ad executive. He’s like the Donald Trump of advertising. (noticing the blank stare) Never mind. You said you were into art. What’s your favorite period?

Stupid Cosmo Girl: Excuse me?

Me: What’s your favorite era of art? Renaissance, Baroque, Romantic, Realism, Impressionism…

Stupid Cosmo Girl: Oh, I like the Renaissance.

Me: Out of all the art movements why is that your favorite?

Stupid Cosmo Girl: I don’t know. Just a lot of great stuff came from that era.

Me: You probably like da Vinci then.

Stupid Cosmo Girl: Yeah, he’s really good.

Me: (I take a second to reflect on what I’m getting myself into. A girl who supposedly got into marketing because she loves art thinks da Vinci is just good) Yeah, da Vinci was pretty revolutionary. You know he was really into geometry. Looking at his work is like a Where’s Waldo? of geometric shapes.

Stupid Cosmo Girl: (looking lost) Yeah.

Me: (I can’t take anymore of this. I take out my phone and pretend to be reading a text.) Oh shit!

Stupid Cosmo Girl: What’s wrong?

Me: I’m sorry I gotta get going. Ben Bernanke needs a consult on the possibility of a trade war with China. (I down my drink and begin to walk away)

Stupid Cosmo Girl: Wait, what?

Me: (as I walk away) Wikipedia it, you’ll be fine.

And scene. So what did I learn?

1) All dating is prostitution, you just don’t always get what you pay for. Okay, so I didn’t exactly learn that because it’s something I’ve known since I was 16. But the point was hammered down even further. Luckily, walking away from a bad investment is a point taught early in business school.

2) A bottle of Maker’s Mark can salvage a bad night. Followed by The Watchmen at 3am on HBO.

3) Sometimes the truth hurts. In those situations, I recommend lying. Not just because I was trying to spare the feelings of Stupid Cosmo Girl, but because my excuse was more fun than just calling her dumb and then walking away.